Vasopressin v1a antagonists

A c-r12, alkyl technology, applied in the field of vasopressin V1a antagonists, can solve problems such as no reported activity of V antagonists

Inactive Publication Date: 2009-10-21
VANTIA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Not reported V 1a antagonist activity

Method used

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  • Vasopressin v1a antagonists
  • Vasopressin v1a antagonists
  • Vasopressin v1a antagonists

Examples

Experimental program
Comparison scheme
Effect test

Embodiment

[0125] Use the following abbreviations:

[0126] AIBN 2,2′-Azobisisobutyronitrile

[0127] Boc tert-butyl carboxylate or tert-butoxycarbonylamino

[0128] Bu butyl-alkyl residues can be further expressed as n (positive, that is, straight chain), i (iso)

[0129] And t (uncle)

[0130] DIEA N, N-Diisopropylethylamine

[0131] DMAP 4-(dimethylamino)pyridine

[0132] DMF Dimethylformamide

[0133] Et ethyl

[0134] EtOAc ethyl acetate

[0135] HOBt 1-Hydroxybenzotriazole

[0136] HPLC high performance liquid chromatography

[0137] H hour(s)

[0138] Me methyl

[0139] Min minute(s)

[0140] MS mass spectrometry

[0141] NMR nuclear magnetic resonance spectroscopy-unless otherwise indicated, NMR spectra are recorded in CDCl3,

[0142] The frequency is 270MHz

[0143] OVA Ornithine Pressor Oxytocin Analog

[0144] Petroleum ether with a boiling point of 60-80℃

[0145] Ph phenyl

[0146] Pn pentyl

[0147] Pr propyl

[0148] THF Tetrahydrofuran

[0149] Tos toluene-4-sulfon...

Embodiment E1

[0154] 6-Chloro-3-methyl-3,4,9,10-tetrahydro-2,3,4,9-tetraaza-benzo[f]azulene

Embodiment E11

[0156] 5-(4-Chloro-2-nitro-phenylamino)-1-methyl-1H-pyrazole-4-carboxylic acid ethyl ester.

[0157] Add sodium hydride (60% dispersion in oil, 7.28g, 180mmol) to ethyl 5-amino-1-methylpyrazole-4-carboxylate (21.8g, 148mmol) in portions at 0°C. Solution in anhydrous THF. The mixture was allowed to warm to room temperature and stirred for 1 h. A solution of 4-chloro-2-fluoronitrobenzene (22.6 g, 129 mmol) in dry THF (50 ml) was added dropwise. The obtained dark purple solution was stirred at room temperature for 18h and then poured into ice-cold 1N hydrochloric acid. The obtained mixture was extracted with dichloromethane (200 ml×2), and the combined organic extracts were washed with brine and concentrated in vacuo. The residue was purified by flash silica gel chromatography (eluent; 60% petroleum ether: 40% EtOAc) to obtain the title compound (27.5 g, 62%).

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Abstract

The present invention concerns compounds according to general formula 1a . Compounds according to the invention are vasopressin V1a receptor antagonists. Pharmaceutical compositions of the compounds are useful as treatment of primary dysmenorrhoea.

Description

Invention field [0001] The present invention relates to compounds having vasopressin Via antagonist activity and pharmaceutical compositions containing these compounds. The invention also relates to vasopressin V 1a The use of antagonists in the treatment of certain physiological disorders such as Raynaud's disease and dysmenorrhea (primary dysmenorrhea and / or secondary dysmenorrhea). [0002] Priority is claimed for EP Patent Application No. 04104062 and US Patent Application No. 60 / 603557 filed on August 24, 2004. Background technique [0003] Nerve growth hormone (neurophyseal hormone) vasopressin (VP) and oxytocin (OT) are cyclic nonapeptides secreted by the posterior pituitary gland. [0004] Only one OT receptor has been fully characterized so far, while three VP receptors are known. These are named V 1a , V 1b And V 2 Receptor. [0005] Vasopressin acts on blood vessels, where it is an effective vasoconstrictor, and acts on the kidneys where it promotes water reuptake, lea...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/04C07D417/10C07D267/14C07D231/38C07D265/36C07D231/42C07D215/08C07D267/16C07D498/14C07D333/44C07D513/14A61K31/55A61K31/5517A61K31/495A61K31/553A61K31/38C07D223/16
CPCC07D223/16C07D231/42C07D413/14C07D267/16C07D498/14C07D265/36C07D513/04C07D513/14C07D295/088C07D487/04C07D215/08C07D333/44C07D417/10C07D267/14A61P1/08A61P1/16A61P15/00A61P15/04A61P15/06A61P15/08A61P23/00A61P25/00A61P25/14A61P25/22A61P25/24A61P3/00A61P3/12A61P35/00A61P3/06A61P43/00A61P7/00A61P7/10A61P9/00A61P9/04A61P9/12C07D233/16A61K31/495
Inventor R·B·安杰伊A·J·巴克斯特C·希尼M·L·斯托克利M·布里安罗P·赫德森R·汉迪
Owner VANTIA
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